


Blackmailing The Gleeks

by Perversity



Series: The Blackmail Series [2]
Category: Glee
Genre: Blackmail, F/M, Mildly Dubious Consent, Multi, Other, Rape, Threesome - F/F/M
Language: English
Status: In-Progress
Published: 2011-06-12
Updated: 2012-12-01
Packaged: 2017-11-20 00:00:34
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, Rape/Non-Con
Chapters: 7
Words: 20,073
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/579063
Author URL: https://archiveofourown.org/users/Perversity/pseuds/Perversity
Summary: <blockquote class="userstuff">
              <p>After a student finds out Santana's secret, he blackmails both her and Brittany, then sets his sights on Quinn.</p>
            </blockquote>





	1. The First Step

**Author's Note:**

> I wrote this story right after moving on from my Hellcats fic. I kind of liked the whole blackmail angle and I wanted to do it again. In the original idea Brittany wasn't even involved, but it made a lot more sense to include her. How could I leave out two of the hottest girls on the show? This story takes place before Quinn had her accident.

You know, I’ve always been a geek. I play video games, watch anime, and I do great in school. I have absolutely no sex life, mostly because I don’t converse much and I have few friends. I keep to myself and more or less ignore anyone who tries to bother me. It’s not like I don’t want to connect with people, I’ve just never had the patience to learn how. So when the ex-cheerleader, Brittany, starts reluctantly pumping her right hand up and down my shaft it’s an incredible feeling.

Brittany is pretty much the school slut, so getting her into bed isn’t really what one should consider an accomplishment. The true accomplishment is the fact that she has no choice in the matter. Well she has a choice, but doing anything other than what I say could possibly ruin her best friend’s life.

I take great pride in being unnoticed, it lets me listen in on things people want to keep secret. In this case, the blond cheerleader’s best friend, Santana, is a closeted lesbian. In high school, it’s kind of important to keep that stuff private. It’s a little sad how being a slut is considered better than being a lesbian, but that’s just the way it is. At first I didn’t really care. I’m a very open minded guy, and I don’t care what people do with their lives as long as they don’t hurt others.

But as I was looking up porn one night, I came across a video that included a blackmail scenario. It had really bad acting of course, but it planted the idea in my head and wouldn’t allow me to think of anything else. So I watched more videos and read stories, the ideas of what I could do with the information I had almost too pleasing to think about.

Just for fun, I started writing down my ideas, planning what I would do if I wanted to blackmail Santana into having sex with me. But no matter what I came up with, I kept hitting a wall. Santana is pretty shameless but still full of pride. If I tried blackmailing her she just might publicly out herself and get me arrested. So I added her best friend to the equation.

There are already rumors that Brittany and Santana have had sex before, although no one has any real proof. It always seemed like some stupid fantasy the guys thought up. However, with the information that Santana is a lesbian, it’s far more likely to be true. I’ve been able to catch tiny snippets of conversation between those two when passing them in the hall, and if I had to guess I’d say those two are a lot closer than even a sexual relationship would imply.

Brittany is pretty dumb, but she’s also incredibly loyal, especially to her best friend. Deciding to think of my conquest of Santana as a multistep process, I decided that the best solution would be to use the blackmail material on Brittany instead, and then use both the information and Brittany against Santana to make sure it stuck.

I’m normally a nice guy, so the idea of doing all of that was certainly out of my element. But the thought of having sex with not one but two cheerleaders made me abandon all of my doubts and take the chance. I’m glad I did.

“Come on! You’re not being very enthusiastic right now. I guess you don’t care about her as much as I thought.”

The taunt does the trick and she moves her hand faster, shooting little jolts of pleasure up my spine. It’s my first sexual experience, so I’m very sensitive. I struggle to keep my mind clear and watch her face as her fist rapidly pumps my shaft. She’s biting her lower lip, while her eyes try to focus on anything but me, which is a little difficult because I’m actually pretty big in that department.

Not wanting to release too soon by watching too much, I look around the room we’re in. It’s an old classroom that isn’t used for anything more than storage these days. Various boxes litter the room and the light hasn’t been changed in some time, casting a half-dead glow over the area. The sun is starting to set, most of the students having already left for home, but the occasional footsteps can still be heard out in the hallway.

During the sports season this room actually sees a lot of activity, but it’s not unusual for the room to remain unused for weeks at a time. For Brittany, every sound in the hallway makes her nervous, causing her to turn her attention to the door every few moments while her hand jerks me off. For me, it’s a little thrilling to be getting a rather nice handjob from a popular cheerleader at school. The danger of getting caught makes it so much more exciting.

“I knew you’d be good at this. Now start using your tongue. I’ve heard rumors that you can get a guy off multiple times with just your tongue and I want to see if that’s true.”

Her fist stops moving, and she looks up at me with pleading eyes. I’m not going to lie; it really is difficult to be the bad guy when it’s not in my nature. Brittany has been “off the market” for some time, much to the dismay of some of the guys who had sex with her. She has a steady boyfriend whom she really seems to care about, and here I am forcing her to cheat on him. It sucks that she’s collateral damage in my attempt to blackmail Santana.

But looking down at the beautiful blond with her hand still wrapped around my shaft, and that pretty face just an inch away from it, makes it impossible to ignore my base desires. I move my hand to the back of her head and pull her closer, pressing my hard shaft against her face. She tries to pull away but I hold her in place, making her feel the heat of my cock against her skin.

“You don’t only have your best friend to worry about here. You know how quickly rumors spread in this school, considering how often you’ve been a part of them. If someone were to spread a rumor about you giving a guy a blowjob at school, how long do you think it will take for your boyfriend to hear about it?”

I grip the base of my cock and slap it against her face, making her flinch and close her eyes, looking truly miserable and on the verge of tears. For some perverse reason, that only excites me more.

“Your boyfriend may care for you very deeply, but do you think, considering your reputation, that he will believe you over the rumor? And even if he does believe you, he’ll have his doubts. He’ll wonder if you are still the slut you were before. Doubts can erode trust very quickly. Now, decide which is the lesser of two evils.”

Her eyes open and she gives me a sad look, but when she opens her mouth and circles the head of my cock with her tongue, her choice is pretty clear. The feeling of it hits me like a truck and I groan almost too loudly in reaction. I clench my teeth to muffle the next groan when she licks the tip of her tongue just under the head.

I have nothing else to compare it to, so I don’t know if she’s good or not, but it still feels incredible. When her tongue licks up from the base of my shaft circles around the head again, I wind my hands in her hair and pull her closer, demanding more from my reluctant partner. I focus on her again to watch her lick every inch of my shaft, making sure no part was left unattended to.

“I guess the rumors are true. I must say, your boyfriend must really love you. If he can experience your talented tongue all the time and not think about how you became so good because you practiced on so many others, then he really cares about you.”

I have no idea why I’m tormenting her, but I can’t really stop myself and the sudden tears in her eyes thrill me immensely. Despite the incredible amount of guilt and shame she must be feeling, she continues to work her tongue all over my shaft. My groans only seem to make her feel worse, but still she continues. I guess she figures that as long as her boyfriend doesn’t find out about this, then it won’t hurt him.

I have a lot of pride in my self-control, but the sensations are starting to wear me down. Every lick is making my entire body tense up in pleasure, and my balls ache with the demand for release. But I desperately hold it back, struggling to maintain control so I can push things even further.

“Good girl. Now give me one hell of a blowjob. You’ll be one of my first, so make sure to leave a good impression.”

She closes her eyes and leans forward, her hot breathe enveloping the head just a moment before her mouth does. As her lips close around the head, my hand in her hair tightens and I can’t help but push further, making her take more of me inside her mouth. I regain control of myself when she chokes and I loosen my hold on her, allowing her to control the blowjob.

She immediately backs up and slides my cock out of her mouth with a slight pop to pull in oxygen. She looks up at me and I lock my eyes on hers as she takes me in again, closing her lips around the head and sucking on it. The sight of her lips stretching to accommodate my considerable size is almost as good as the feeling itself.

It’s almost disturbing how quickly I start to lose control over myself. I try to reason that I’m just a virgin and this is my first sexual experience, while Brittany has been doing this a lot longer, but I can’t help but feel ashamed of my lack of control. I’m certain it will improve over time, but I’m still not pleased about it.

“Tell me something, Brittany. Is it true that you’ve fucked most of the football team?”

She closes her eyes again in shame but slowly nods. The fact that she’s doing it with half my cock buried in her mouth sends pleasurable sensations up my spine, making it difficult to think clearly.

“Are you ashamed that you were so easy to get into bed? I mean, you’re known as the school slut. Most of the guys in this school only want to be with you because you’re a sure thing.”

She nods again and I smile down at her. I know she’s been trying to change and move on from the type of girl she used to be, so reminding her of all that is no doubt causing her a lot of inner torment. I suppose she has learned what kind of relationship she can have with a guy who genuinely cares for her, and she doesn’t want to go back to being the slut that everyone remembers her as.

But here she is, sucking off some guy in a storage room. She’s not doing it willingly, but the fact that I’m enjoying it so much is because of her vast experience with other guys. Tears slide down her cheek and it doesn’t help when I tell her to keep sucking. She immediately starts bobbing her head up and down my shaft, keeping up almost continuous suction.

I slowly reach the back of her mouth and butt up against her throat. Not even needing to tell her to do it, she starts to swallow me down her throat. The feeling of it nearly sends me hurtling over the edge, and I have to run a bunch of non-sexy images through my mind in order to prevent myself from blowing my load right then and there.

She finally stops about a couple of inches away from the base of my shaft and stays still, working her throat muscles around my cock. That is way too much for me to handle. I once again tighten my grasp in her hair and hold her in place, only pumping my hips a couple of times before I finally release my pent up semen down her throat. She only briefly struggles against my grip, trying to rise up and off my cock, but she quickly has to divert her energy to swallowing each spurt of cum that slides down her throat.

It’s the hardest I’ve ever come in my entire life, and my mind blanks completely as I force her to drink every drop. When she swallows the last of it, my grip on her hair loosens and she immediately pulls back, gasping and coughing for oxygen. I stare at the blond girl for a while until I am able to focus again. My cock softens very quickly and I know that even if I want to, there’s no way I can go another round after that. Not yet anyway.

“Are we done?”

Her breathing is under control, but her voice is hoarse. For some reason, it pleases me to know that she can hardly talk right now because of me.

“For tonight. I’ll contact you tomorrow and tell you where to meet me.”

She can’t possibly think this is going to be over after just one blowjob. You would think her experience with men would show we’re definitely not satisfied with just a blowjob when we can get more than that. There are a lot of things I want to do to my new sex slave before I bring Santana into this. I need her under my full control before I take the next step.

“You should probably go and spend the night with your boyfriend. After tomorrow, you’re going to have a lot more to feel ashamed about.”


	2. Sex With A Cheerleader

**Summary for the Chapter:**

> The student has some firsts with Brittany.

I have to say, it’s odd how much of a confidence boost I got from the act of controlling the beautiful blond. I barely got any sleep that night, the entire experience replaying in my head time and again until I had every moment, every sensation memorized. The knowledge that I would get even more the very next day didn’t help my normal amount of insomnia one bit.

However, it also made me very paranoid. What I’m doing is not only morally wrong, but also extremely illegal. I forced myself to act completely normal during breakfast the following morning, a ritual I rather enjoy having with my single mom and little sister. My dad was never in the picture, not because he abandoned us or anything but because not even my mom knows who he is. My mom was apparently quite the wild child, and that side of her never really went away.

Normal people might say that’s not a good thing, but she’s a loving mom. We’ve never been neglected and she raised us to have an open minded view of the world. She claims my sister and I were happy accidents, although I can tell it’s really tough on her sometimes. I help out wherever I can, but she insists that we focus on school. She’s a strong woman whom I really love and respect. She works as an assistant at an accounting firm. It pays well enough, so we’re never strapped for cash.

My little sister is sweet, but she’s right on the cusp of that age where she starts to hate everything. It annoys my mom to no end, but I think she’s hilarious. We’ve always been close, but she has her own mind, and her strong, independent nature is definitely a trait passed on from my mother. She’ll come to me when she really needs help or advice but handles everything else on her own.

Considering my rather normal life, it baffles me how I could spend the entire school day thinking of how I wanted to dominate and fuck my new…sex slave? Is that a proper name for what she is now? I guess I’ll use that for now until I can come up with something better. It’s just that so many TV shows and books have lead me to believe that if you do what I’m doing, then you have to be pretty screwed up with a broken home life and mommy issues.

Perhaps it’s merely a case of a geek getting to use a really hot cheerleader as his plaything. In my situation, what geek wouldn’t take this chance? I guess those on a moral high horse, but a majority of us would see what we could get away with. Or maybe I’m just trying to justify the fact that once this school day ends, I’m going to lose my virginity to a girl who has to do everything I say.

At the end of the day, I’m sitting in the cheerleader’s locker room, patiently waiting for her to arrive. Before sending her home the night before, I instructed her to meet me here at nine-o’clock sharp. At this time in the evening the school is completely empty, leaving only dark hallways and complete silence. It’s oddly amusing how creepy a high school is at night.

I turn toward the door when I hear it open, and in comes Brittany, wearing her cheerleading uniform just as I told her to. I know it may be a little cliché but it’s a fantasy, so sue me. Damn, I had forgotten how good she looks in her uniform. She has one of the best bodies in our school, and while the uniform is pretty modest, my eyes are often drawn to her strong looking legs. They look like they can wrap around you so tight you’ll never escape. But then again, who would want to?

She seems to grow more uncomfortable with each moment I just stare at her. She looks like a deer being stared down by a hungry predator. I suppose you can classify me as such.

“Hello again, Brittany, I half expected you not to show up, in some foolish attempt at disobedience. I guess I overestimated you a bit.”

The jab clearly stings her, as it was meant to, and I’m treated once again to the sight of her shame. I like seeing that more than I ever thought I would. For some reason it’s a lot of fun to make her feel like shit.

“If I don’t do as you say, you’ll hurt Santana.”

As if that’s reason enough, she doesn’t elaborate. I smile then close the distance between us and wrap my arms around her, pulling her body against mine. She tenses up, but even through her uniform her excellent body molds against mine and I can feel her firm breasts pressing against my chest.

“However, if you do as I say then I’m going to make you cheat on your boyfriend in every way imaginable.”

I slide my hands down her back and reach under her skirt, then cup her taut ass in my hands and squeeze the firm globes, pulling her closer so that she can feel the bulge in my pants. Nothing has really happened yet and I’m already hard for her. Hell, I’ve been hard as a rock for most of the day. Thank God none of the teachers asked me to stand up. That’s one high school cliché I never want to join the ranks of.

“And I’ll likely not hesitate to have my way with you before going to your Glee class every day. Tell me, can you look your boyfriend in the eye right after you fuck a different guy?”

Pressing against her as I am, I feel her entire body shiver as I force those images into her mind. I expected revulsion, but a shiver? That might make things even more interesting. I’ve always had my suspicions that she might have actually enjoyed all of her sexual encounters even if she didn’t like the reputation it gave her. From the things that I’ve heard about her, she’s very enthusiastic in bed. It could be typical guy-talk bullshit, or it could be the truth.

I lean forward and claim her lips with mine, forcefully drawing her into a passionate kiss that she has no choice but to respond to, while my hands continue to grope her firm ass and rub her against my clothed penis. The feeling is intoxicating, the way her slender form molds against mine, the feel of her ass in my hands, the way her lips respond to the kiss between small gasps of air. But with each grind against me, the pain of being constrained in my pants sobers me up pretty quick. It’s time to fix that.

I reluctantly pull away from the kiss, taking note of the somewhat distant look in her eyes, and slide my mouth down to lightly nibble on her neck.

“You know what I’m going to do with you right?”

I keep the question just above a whisper, and the feeling of her body shivering against mine as she no doubt pictures it gives me the answer I’m looking for before her words do.

“You’re going to have sex with me.”

I shake my head and move my hand around to her front, then slowly rub two of my fingers against the front of her panties. She bites her lower lip and is almost able to hide the gasp, but I still hear it loud and clear. With every passing moment she confirms my suspicion that she was a slave to her desires long before becoming a slave to me. I need to push a little harder to be absolutely certain though.

“No I’m not going to have sex with you, Brittany. I’m going to fuck you. I’m going to slide your panties off your body, press you against the nearest surface I can find, and I’m going to take you.”

Her teeth worry at her lower lip so hard I’m surprised she doesn’t draw blood. Her eyes close and I feel her pressing against my hand, whether she knows she is or not. I wonder if there is a masochist in her as well. I can’t decide what I like more. The idea of sexually dominating a helpless cheerleader, or making her come her brains out and then making her feel like a whore because of it. I guess I’ll continue and see where this leads.

“I can’t see you being completely satisfied by those idiots you fucked before. You always wanted more right? They would always finish far too soon and you’d be left with the feeling of wanting to be taken even harder. I can take you harder right now.”

I’m pretty much just making this stuff up as I go along, but I apparently hit the nail on the head because her body suddenly shakes just a bit, and I feel a light flood of her juices coat my fingers. Damn, apparently the visual was a little too much for her! She loses her balance and leans her head on my shoulder, slowly recovering from the orgasm I just gave her. Goddamn it’s one hell of a sight watching her release like that!

I wait until her breathing returns to normal then grab her hand and press it against the front of my pants, making her feel how hard I am. Seemingly working on automatic now, she lifts her head and looks me right in the eye when her hand suddenly rubs against me, gripping me as much as possible through my jeans. I gasp in response, half in pain and half in pleasure. I remember how good her hand feels around me all too keenly.

I’m glad she’s getting into this a lot more. Fucking a reluctant and/or crying girl isn’t my idea of a good time. If she’s far more willing and even participates, the experience will be a lot better for the both of us. Still, there’s a distant look in her eyes, as if every other thought is a million miles away and her desire has taken hold of her. I’m certain she’ll return to her normal state of mind when this is all over, but right now she’s an eager sex slave.

I feel her tugging at my pants, and let out a loud sigh of relief when her hand fishes out my cock, freeing it from its painful restraint. She gives my shaft a long, hard stroke from base to top and then back to the base again, making me groan and surge forward. It would seem that all of this anticipation and watching the blond come all over my hand has left me right on the edge. Damnit!

“You’re too close. I can take care of this if you want.”

Her grip tightens a little around my shaft as if to prove a point. I don’t trust my voice, so I merely nod at her and watch her drop to her knees. One thing I came to accept the night before is that I absolutely enjoy seeing her on her knees pleasuring me, and this time is no exception. No doubt knowing what she needs to do, I watch intently as her lips quickly suck the head of my cock inside her mouth and then swallow half of my shaft within just a few moments.

The pleasure rips out a most unmanly sound from me, and I wind my hands in her long hair again, even if only to have something to hold. Since the eager slut is doing great without any guidance from me, I don’t influence her movement in any way, just choosing to lean back against the nearest wall and enjoy. Her head bobs up and down swiftly on my cock, each time drawing me just a little deeper inside her throat until her nose finally presses against my pubic hair.

Her throat constricts around my cock and she raises a hand up to fondle my sensitive balls. That’s finally way too much for me to handle, and I release down her throat almost immediately. Still allowing her to control the pace, her head continues to bob and suck, her wicked little tongue slithering around my shaft and she somehow manages to swallow every drop I pump down her throat. It’s a glorious feeling when her mouth slides off my shaft and I bask in the aftermath of my release.

I’m still recovering when her face moves close to my shaft again and her tongue circles the head of my dick, lapping up what’s left of my semen and keeping me hard in the process. It’s not difficult to imagine why so many guys like fucking her. After a few minutes of her eager tongue bath, something I was in no real hurry to stop, she finally pulls away and stands back up.

I look her in the eyes again and see the same distant look, but there is also very strong arousal. I don’t need to be experienced to see that. Deciding it’s time to get underway, I cross the room and grab one of the chairs then place it right in front of Santana’s locker. I quickly remove all of my clothes before I sit down and motion for her to come to me. As she stands before me once again, she notices the name on the locker and her reluctance returns almost immediately.

I decide to ignore it and reach forward, then hook my thumbs inside her panties and pull them down her slender legs until they drop to the floor. Damn, she looks so hot standing before me with no panties on but still wearing her uniform. Seeing that gives me a dirty little thought, and I decide to mess with her head a bit.

“You can still stop this you know. You can pull your panties back up and leave this place right now. I will still leak the information about Santana and also reveal everything you and I have done so far, and she’d have a really tough time of things, but at least you wouldn’t have to cheat on your boyfriend and degrade yourself even further. From what I hear, your boyfriend is the first guy who has ever seen you as anything more than a good lay.”

I stroke myself as I taunt her, making it awfully clear what the next step is in all of this. I mean it though; if she wants to leave I won’t stop her. I feel like she needs to be the one to take the next step if I’m going to proceed to the one after that and get Santana involved.

“I suppose he saw something special in you. Maybe he thought you could change and become a young woman who is proud of herself. But you haven’t changed have you? You’re still the same eager slut as before, and the only thing special about you is how good you are at being one. I guess it all comes down to a very simple decision. Are you going to fuck me to protect the people you care about, or will you walk out and risk losing it all?”

It doesn’t take her as long to decide as I thought it would. She closes the distance between us and lowers herself onto my lap, poised right above my cock. I grasp her firm ass cheeks in my hands and squeeze them, making her lean forward so her chest is pressing against mine. I prod her wet opening with the head of my dick, teasing her.

“Are you a slut, Brittany?”

She looks down at me and slowly nods. I press against her opening again but rub against the sensitive hood of her clit. Her breathing hitches at the contact and I can’t help but smirk up at her.

“Don’t nod; tell me in your own voice! Are you a slut?”

“Yes…I’m a slut.”

I barely hear her, and saying the words aloud only seems to make her feel worse. After seeing how quickly she gave in to that lust before, I have no doubt that once we get started she’ll be very eager again. I’m doing this just for my own amusement.

“Your boyfriend deserves someone a lot better than a girl who is so easy to get into bed, doesn’t he?”

She nods again, and then suddenly gasps when I squeeze her ass and rub my cock against her clit again. Her shame and humiliation is warring with her desire. Her body wants what it wants, and she is still so used to obeying it over everything else. I want the slut in her to overcome the person she was trying to become, and I want her to know that it’s happening.

I draw her down into a kiss, making sure to give her mind something else to focus on. It’s only natural to run away from an uncomfortable feeling. People hide their pain all the time be seeking solace in sex, and she’s no different. She responds to the kiss and pulls me closer, pressing her body against mine to increase the contact.

I pull away when breathing becomes an issue and we just stare at each other for several moments. I nudge my cock against her wet opening again and she seems to come to a decision. She wraps her arms around my neck and shifts to a more comfortable position in the chair. Poised just above my thick shaft, she slowly lowers herself onto it. When the wet heat of her sex envelopes the head, I clench my teeth together and catalogue each new sensation as she takes more of me inside.

Surprisingly enough, she’s pretty gripping me very tightly. It could be because I have a big dick, or because she always takes really good care of her body. Either way, when she finally settles down against me with every inch buried inside her, I groan out the breath I didn’t know I was holding and take a few moments to admire the feeling and sight of the uniformed cheerleader on my lap.

Sometime during her descent, she had closed her eyes, and right now there’s an intense look on her face. I squeeze her firm ass again and she lets out a sexy little whimper and clamps down around me, sending little lightning bolts of energy throughout my body and melting every nerve ending I have. Her eyes open again and I’m almost floored by how intensely aroused she looks. Her body is calling the shots again, ignoring everything else but what she wants.

“Show me why most of the guys in this school can’t get enough of you, Brittany.”

In response, she does a sexy rolling thing with her hips that makes me groan and tilt my head back. She then slowly draws herself up until I’m halfway out of her and swiftly pushes back down. Our moans of pleasure start to mix together as she sets a steady, riding pace. Every time I grope and squeeze her ass, she tightens around me, causing an incredible messaging sensation along the length of my cock.

I don’t know when it happens, but I start raising my hips up to meet hers with every downward thrust, making her cry out in pleasure every time I enter her. In response, she speeds up her own thrusts. The slap of flesh against flesh becomes almost as loud as our moans. She’s quite vocal about her pleasure, and I’m enjoying seeing her this way. I kind of wish I hadn’t asked her to wear the uniform, but it’s definitely one hell of a sight.

Unfortunately, I’m not nearly used to this enough to control my release for very long. Every time I feel her take every inch of my cock inside of her and hear those sexy moans, I very nearly topple over the edge. It’s becoming damn near painful!

“I’m close!”

I warn her because if she doesn’t come as well, I’m going to be very disappointed. She suddenly slows down and leans back a bit, instead of leaning mostly against me like she has the entire time. She pulls up until only a little of shaft is out of her and then slams down hard. My sharp moan causes her to do it several more times before she makes me come. Just as I release inside of her, I feel her entire body convulse while she whimpers. She worries at her lower lip again with her teeth, and I enjoy the sight of her tensing up with every stream of semen I shoot inside of her.

When both of our orgasms finally stop, I lean back in the chair and try to catch my breath. Seeing that she doesn’t have anything else to rest against, I pull her against me until she finally surrenders and rests her head against my shoulder.

Oh, Brittany…you have so many things to teach me.

**Notes for the Chapter:**

> I wanted to portray Brittany as a reluctant slut more than a victim. I prefer writing psychological pain over physical pain, so I don't do beatings or anything. It's just not my style. The chapter always felt a little rushed to me and I probably should have extended it a few pages but this is what I released.
> 
> More and more you'll see that while this character shares many similarities with the Professor from my Hellcats story, their wisdom on the practice of blackmail is vastly different.


	3. Breaking It Down

**Summary for the Chapter:**

> The student's plan to ensnare Santana falls together.

Let me tell you, having sex regularly with a young woman who is in excellent physical condition is a great way to learn how to have sex. It has been a month since the first time we had sex and I’ve used every day of that to learn how to pleasure a woman. Brittany has more or less grown accustomed to being my sex slave, and she no longer gets deeply upset when we have sex. It’s more like she has separated the part of her that likes the sex and the part of her that is trying to become a better person.

It utterly confuses me how some guys can get laid all the time and still be so terrible at it. Having sex every day and sometimes even more than once, for an entire month has made me quite good at it. I’ve always been a quick learner, taking much less time to understand something than most others, so maybe that has something to do with it. Brittany is also kind of a nympho, and my pride won’t allow me to finish before she does.

I’ve learned how to control myself quite well, so I don’t blow my load too soon, which is really a challenge because the blond is so damn good at what she does. More than once I asked her to keep me on the edge as long as possible, so I can learn how to keep a level enough head. I’ve also returned the favor on many occasions, oftentimes only focusing on pleasing her. In a month I’ve gone from a sexually naïve virgin to a pretty good lay. Considering how experienced Brittany is, I consider it an accomplishment.

There’s a reason why I’m spending all of this time trying to become better at pleasing a woman. When I finally take Santana I need to make sure she feels good no matter how much she hates what is happening to her. Being as experienced as she is she probably won’t hesitate to tell me I suck if there is any possibility of hurting my ego. This way, her body will be honest even if she’s acting like it’s not effecting her.

However, the blackmail material I have on her isn’t nearly enough to guarantee her compliance. As I mentioned before, Brittany is the key, but she’s only useful to me as long as I use that key. This is why she’s currently looking up at a camera, her mouth wide open, as I release a load of semen all over her pretty face. Her hand swiftly pumps my shaft, eagerly milking me of every drop. Only a little of it actually lands in her mouth, with the majority of it covering her face and hair.

It’s not a small release, the rest of the video containing almost two hours of sex leading up to this moment. It was more difficult than you can possibly imagine to hold it back that long, but there’s a purpose to it. After the last stream of cum hits her face, she licks my twitching shaft and sucks one last time to make sure she has it all.

“Good girl. Now what do you say?”

She swallows the semen in her mouth and looks directly at the camera again.

“Thank you…”

“Good. Now go get yourself cleaned up. School starts soon and we don’t want to be late now do we?”

She shakes her head and stands up, crossing the room to the bathroom. I record the sway of her shapely ass until she disappears from my sight. Just to be clear, the camera I’m holding is not one of those low quality cameras that you see so many times during crappy sex tapes and home videos. Oh no, this baby records in full 1080p. I’m a bit of a tech geek, so when I finally decided to start recording our sessions, I brought along a camera that records in excellent detail.

We live in a High-Def world ladies and gentlemen; shitty $100 cameras are no longer acceptable. Everything about filmmaking these days is about high definition, and it’s startling how many people still buy the worst cameras possible to record their intimate moments. I make it a point to keep up with the latest tech, and if I have the money for it, I buy it. I don’t always have a practical use for it but I like to keep up with the times.

Using this, I’ll be able to take the next step today. A month is long enough, and I can’t keep putting it off because there’s no telling when she’ll just come to her senses and come out of the closet on her own, which would remove Brittany’s reason to follow my orders and put a stop to everything. Getting to Santana will tighten my hold over both of them. In the end, they’ll turn into each other’s blackmail.

But first, I need to show Santana a little video…

\------------------------------------------------------------------

End of the day…

I can see Santana reading the note I left her after school. I tried to mimic Brittany’s handwriting as much as possible, but it’s really not something I’m good at. The note merely tells her that they need to talk and they should meet at Brittany’s house. She’s not going to be there of course, she has some kind of date with her boyfriend, and over the last month I’ve memorized the time when her parents are home. They won’t be back until late.

I’m a little surprised when Santana approaches the front door, and instead of knocking she pulls out her own key, unlocks it, then walks right in. I wonder if Brittany has a key to her house as well. Slowly, ever so slowly, I’m learning the full extent of their relationship. Anyway, I had spent some time setting up the scene in the house. Immediately as she enters, she’ll hear the shower running upstairs. I turned it on because I didn’t want her calling out to Brittany. If no one answers, she might just leave.

Outside of the house, I give her a couple of minutes to walk upstairs before I enter as well, moving as quietly as I can. If she hears me at all before she gets to Brittany’s room, the entire plan is a failure. When I hear her footsteps reach the top of the stairs and enter the room, I slowly follow her up. I know the layout of the house pretty well by now, and while Brittany has her own bathroom, you have to cross her room to get to it.

When I hear the sound of her feet walking on tiles, I quickly enter the room and move over to the side, slipping inside the closet. I thought about merely being in there from the start, but I couldn’t run the risk of Santana taking a quick look around and spotting me in there. The plan would be ruined even worse if she finds me in her best friend’s closet.

“What the hell?”

I hear her voice echo out of the bathroom and the shower turn off a moment later. I can’t help but wonder if Santana was hoping to catch her friend in the shower. Heh, I’ll indulge in that fantasy another time. I made sure to keep the room mostly dark, but the bathroom lit up. When she finally exits the bathroom and returns to the room, she sees the reason why. Over by the door on a desk is a laptop, one she didn’t notice when she entered because I kind of put it out of the way. Besides, who would expect a computer in Brittany’s room?

She curiously crosses the room and notices the cd tray is ejected, with a cd still in it. From what I’ve learned of her, she likes to snoop around a little too much. There is nothing written on the cd to give her any indication of what it might be, so of course she’s going to close the tray. When she does, a media player recognizes the video and starts playing at full screen. Brittany’s face appears on the screen.

“Tell the camera what you are, Brittany.”

Santana sits down in front of the screen and openly stares when the camera zooms back; revealing that the blond is completely naked and sitting in the chair she’s in right now.

“I’m a slut.”

Santana’s eyebrows rise up just a bit and I watch as she shifts uncomfortably in her chair.

“Do you like being a slut?”

She shakes her head and I laugh at her in the recording.

“You seem to like it to me. You say you’re doing this to protect Santana, but you’ve been quite the eager little slut this entire month.”

At the mention of her name, Santana’s reaction is almost instantaneous. She gasps and even I can see the tears in her eyes from here. But for some reason she keeps watching.

“I’ve fucked you every day for an entire month. You’ve swallowed so much of my semen I seriously doubt you’ll ever forget the taste. I’ve made you cheat on a boyfriend who adores and used you relentlessly for my amusement. You must care about her a lot.”

Brittany looks down away from the camera and mumbles something, but I pick it up easily enough.

“I care about her more than anyone.”

Immediately after that it transitions forward, showing Brittany facing the camera on all fours and moaning as I ram myself inside of her. I wind my hands inside her hair and grab one of her hands, using both as leverage to pull her back on to me with each thrust. She’s clearly enjoying herself, much to Santana’s obvious dismay when she quickly snaps the laptop shut. Perhaps I laid it on a little too thick, because she’s outright crying now. I try not to enjoy her torment too much. I seriously don’t know why I get off on it as much as I do.

“Stopping already? But there is so much more left to see.”

I step out of the closet and she immediately swirls to her left and glares at me. Her next action is entirely unsurprising and she immediately crosses the five or so feet between us and tries to hit me. I’m no fighter, but the swing is more than a little wild and I step aside and dodge it easily. Not one to give up, she swings again but the short distance between us allows me to quickly close in on her and use my form to pin her body to the wall. Being wary of her hands, I grab both of her wrists and with a lot of effort manage to pin them to the wall as well.

“You son of a bitch!”

She tries to get herself free but she’s pinned pretty good, and my laugh only renews her struggle to free herself and likely kill me.

“I would calm the fuck down if I were you! With the recordings I have of Brittany, she’ll barely be able to have any life at all!”

She stops struggling when she hears that threat, but if her glare was a physical force I would be flayed alive. I have to admit, I find her attitude endearing.

“Good girl. Now, we need to have a little chat about Brittany. If you get violent I won’t hesitate to put that video online. Once something like that reaches the internet, it stays there forever. Considering how much your best friend did just to keep your secret, it would be terrible to not control your anger and help her. Understand?”

She nods, but it’s difficult to tell if she’s being truthful, because she’s also glaring daggers straight through me. I decide to take that chance and move step back from her and release her hands. For a moment it looks like she’s going to swing again, but I guess she decides against it and rubs her wrists instead.

“What the fuck have you been doing to her?”

I can’t help it; I laugh and briefly look back at the laptop.

“I think the video was pretty self-explanatory.”

She clenches her fists and almost lunges at me, but somehow keeps herself under control.

“Why did you show this to me? It sounds like you were getting away with it.”

I grin at her and casually walk over and sit in the chair, then open the laptop and turn the screen toward her. The video is stuck on Brittany’s moaning face. I point to her on the screen.

“Because this was never about her, she was just a convenient tool to get to you. Knowing that you’re a lesbian isn’t enough to insure that you’ll do what I say. However, if I use the girl you no doubt love against you, then you’ll have no choice.”

I press one of the keys and the video starts playing again. Brittany’s moans and the sound of skin slapping against skin fill the room. Santana looks away from the screen, and the tears that never really went away start to flow again.

“So you just used her. I may be a bitch but she’s a good person!”

I click near the end of the video and pause it on Brittany’s semen covered face.

“She’s a slut, just like you, so I used her like one. I never physically harmed her or caused her pain. I’ve become so good at making her come that it hardly takes any effort at all anymore. It’s not like she’s faking the pleasure in this video. When I fuck her, she fucks me right back.”

I stand up and bring the laptop with me, holding the screen in front of her face.

“But if she had any actual choice in the matter, she wouldn’t keep doing it. She’s been doing this because of you.”

Taking advantage of an emotionally weakened Santana, I grab the back of her head and force her to look at the semen covered image of the woman she loves. She tries to pull away, but it’s like all the energy in her body has left her.

“She’s willing to be treated like this because of you. If this gets out, her entire life will be defined by it. She may be a little dumb, but even she’s smart enough to know that. So it all comes down to one very simple question.”

I snap the laptop shut again and toss it onto Brittany’s bed. I close the short distance between us, and with my hand still on her head, I force her to look at me.

“How far are you willing to go to keep her secret?”

**Notes for the Chapter:**

> This one had almost no sexual content of any kind. Chapters three through five were actually one chapter that I cut apart to keep the chapter lengths as even as possible.
> 
> I didn't have any problems with this chapter after I finished. I like how I wrote it and I think it served its purpose. I wanted to focus on tormenting Santana first.


	4. Oral Examination

**Summary for the Chapter:**

> Santana experiences the fruits of his labor.

We stare at each other for a good thirty seconds, her stubborn glare meeting mine. If she doesn’t go through with this, at least I’ll have what I need to make Brittany my willing sex slave for as long as I want, but if she agrees then I’ll have two smoking hot cheerleaders to do whatever I want with. Come on, what would you readers want in my position?

“Your decision has a time limit, Santana. If you don’t make your choice, I’ll wait here until Brittany comes home and spend the next few hours using her as I please. However, if you put aside that pathetic pride of yours and decide to help your friend, then you will replace her for tonight. Either way I get what I want, the only thing that is undecided is from whom.”

I take a quick look over at the laptop and she closes her eyes.

“Fine. You can play your sick game with me tonight. Just leave her alone.”

I can hear her teeth grind together in anger and she pretty much spits out her response, but it’s still a decision nonetheless. I grin at her then let go of her head and step back.

“Good girl. Now remove all of your clothes, I want to get a good look at my new property.”

Referring to her as my possession gets her visibly angrier, when she clenches a fist at her side, but she does what I say. I’ve heard that while she’s not as physically fit as her blond friend, she’s much curvier. This girl wears tight jeans and form-fitting dresses that accentuate her form all that time, but the real thing beneath the snug wrapping is a lot better than anything my imagination has ever thought up.

She pulls her top over her head and tosses it aside, revealing she’s not wearing a bra. I suppose she thought it would be coming off tonight anyway. Her breasts look like little more than a handful, but they fit her figure. I don’t care about the size of a woman’s breasts, they’re not what turns me on about them, but there is such a thing as the wrong size. For me, the breasts need to fit the body, and they really do fit Santana. When she attempts to push down her tight pants I stop her.

“Turn around. I want to see your ass when you push them down.”

She rolls her eyes but does as she’s told, and I sit down on the bed almost right in front of her ass as she pushes her pants down, her red silk panties with them, then bends over to push them the rest of the way. I’m not ashamed to admit that I’m an ass guy. A nice ass is a turn on for me, and I have to say it’s her greatest feature.

Brittany also has a good ass, but Santana’s is curvier and looks taut. I can’t help it; I reach forward and squeeze both of her ass-cheeks with my hands. She gasps in surprise and stumbles just a bit before regaining her balance and glaring back at me. Oh yes, definitely a firm ass. Brittany’s ass is a little more pliable. I squeeze them again and smirk at her when I feel her body tense up. The look in her eyes tells me she want pummel me into a fine paste, but she knows her place and doesn’t do it. For now, at the least.

“You really do have a fine ass, Santana. Many of the guys you’ve slept with have expressed disappointment in the fact that you don’t do anal.”

I pull apart her cheeks and notice she doesn’t have hair anywhere. She shaves pretty much everywhere, leaving only smooth curves of skin. She really is a very beautiful girl; it’s no surprise why so many guys go after her. I feel a shudder run through her body as I study and squeeze her ass, and when I look at her face, she doesn’t succeed at hiding her expression fast enough for me not to notice her biting her lower lip. Even if she had managed to hide her expression, the light moistening between her thighs would have given her away very clearly.

“I suppose that even when you’re a lesbian, you can still be a slut. I’m squeezing your ass and here you are, getting wetter by the moment. You and Brittany aren’t making the best case for the belief in change here. Brittany’s been trying to change her slutty ways, yet when you get her turned on she turns into a complete whore, and you’ve been far less sexually active after becoming a lesbian, but your body still seems ready for a good fuck at a moment’s notice.”

I can almost hear her gritting her teeth again in anger, but she only seems to get wetter. I decide to see how hard I can push her and slap bring my hand down with a loud slap against her ass. She cries out in surprise and pain, but doesn’t have time to react before I slap the other cheek. After a few more sudden slaps, her ass turns a very light shade of red, which really contrasts with her skin. Santana isn’t too happy, of course.

“You son of a bitch! I’m gonn-AH!”

I slap her ass rather sharply before she can finish her threat. When she looks behind her to look at me again, I fix her with a glare that makes even her retort die on her lips.

“You’re going to what, exactly? You don’t seem to grasp the reality of your situation, so let me put it plainly for you.”

I make sure to sound as cold as possible, and to make my point I lower one of my hands and rub two of my fingers against her moist slit. Apparently sensitive to my touch, she gasps a bit and hangs her head.

“I don’t give a shit about your pride, and your tough girl act is only hilarious when you’re bent over naked in front of me with a wet cunt. You belong to me now, which means I can do whatever I want with you and you have no rights to anything as my slave, least of all your freedom of choice. If you continue to give me problems I’ll just tie you up, hide you in that closet, and make you watch as I fuck the woman you love tonight. Are we clear, or do I need to grab the rope?”

I make my tone sound as threatening as possible, which is difficult since I’m not really that frustrated with her, but she needs to get it through her head that she’s mine now, I own her. I watch as many emotions flit across her face, including the strong emotion of sadness when I threaten to fuck Brittany right in front of her. There’s my opening.

“If you behave, then I’ll give Brittany to you. You two haven’t been able to have sex since she got a boyfriend have you? Follow my orders and you can have her. Disobey my orders and I’ll make sure everybody has her.”

It doesn’t seem to take her very long to decide, as she suddenly stops fighting against me and relaxes her body. I rub my middle finger against her clit, making her entire body shudder as it responds to the stimulation. Wow, I guess going from a girl who had sex all the time to a girl who has sex only very rarely has done a number on her libido. She may be a lesbian now, but her body still responds like before, no matter who is causing it.

“Lay down on the bed and spread your legs.”

I stand up with the laptop in my hand and cross the room from the foot of the bed while she follows my order. I open the laptop again and move to a part in the video where Brittany is laying in the same position and hit the play button. I return the bed and crawl over between her spread legs, resting my hands on her knees to make sure she doesn’t try to close them. Apparently she expects me to just mount her and get to it, because she looks surprised when I lower my head and firmly lick the very tip of my tongue from the bottom of her slit all the way up to her clit.

When I circle my tongue around the sensitive bundle of nerves, she lets out a sexy gasp and involuntarily raises her hips to increase the contact.

“Oh, my God!”

I hear Brittany’s voice from the video suddenly, followed by a long drawn out moan. In the video, I’m doing much the same thing to Brittany that I’m doing to Santana right now, and as I look up at her, I see that she’s trying and failing not to look at the video as her best friend responds strongly to my mouth.

“I swear, Brittany is addicted to oral sex. She doesn’t need a dick at all to get off, just stick a tongue inside of her and she’s happy. I suppose you played a role in that, didn’t you?”

Being a guy who believes in equal pleasure, I spent a lot of time practicing my oral skills on Brittany. Seeing as she is addicted to it, I could literally bring her to several orgasms before either of us got tired. At first it was difficult because my mouth got tired, but the more time I put into it the more I learned to pace myself. That’s why it takes me only about thirty seconds to have the far more experienced Santana gasping and shuddering repeatedly with each stroke of my tongue.

She was wet before, but now she’s soaked, and her entire body signals a release of more of the nectar whenever I wriggle my tongue inside her. Her gasps become quick intakes of breath each time I focus on her clit, and those sounds are interrupted by sharp moans of pleasure that I can tell she’s trying to hold back. I periodically look up at her face, enjoying the sight of her mouth hanging open and letting out sexy sounds, and those beautiful eyes flicking between the computer screen, myself, and closing to process the pleasure.

Her hands grasp the blanket beneath us hard enough to almost tear the fabric. Deciding that I no longer need to hold her legs apart, she’s doing that all on her own now, I slowly slide my hands up her legs and across her smooth torso and take her breasts within my hands. They fit in my hands quite nicely, and as I test their firmness I squeeze her small nipples between my fingers.

“Ahh!”

She lets out a sharp, quick cry but the breathy moan that follows and the shuddering of her body is anything but fast. Knowing an orgasm when I feel one, I greedily dig my tongue as deep inside of her as I can and lap at her inner walls, drinking down her tasty release. I don’t think even she notices, or cares for that matter, when her hand lowers and insistently pushes at my head, demanding more. Even when her juices slow to a stop, she doesn’t come back down because I keep her right where I want her.

I alternate between squeezing her lovely breasts and lightly twisting and pulling on her rock hard nipples. Combining that with my mouth practically feasting on her eager sex and she falls over the knife’s edge again rather quickly. When I feel her approaching her second orgasm, I slide one hand quickly down between her legs and slide two of my fingers deep inside of her, hooking them just a bit to rub against her inner walls.

Her body arches and pretty much lock in place, the swipe of my tongue across her clit sending her screaming over the edge once again. She clamps down around my fingers with a surprisingly vice-like grip that prevents them from moving out of her. Instead of lowering my mouth to sample her release again, I keep my tongue focused on her clit, which is apparently where she wants me because her hand holds me in place with an unyielding grip, and her hips twitch quite erotically each time she feels my tongue.

When her body rests back down on the bed and her orgasm stops, I pull my fingers out of her and give her slit one last lick before pulling away. I would continue this even longer, but Brittany will be back at some point and I don’t want her to know of Santana’s involvement until I get what I want from her. I move up her body, allowing my hands to explore as I please until I look her directly in the eyes.

“Now you’re going to return the favor. I’ve heard rumors that you have quite the talented mouth, and I’m dying to know just how talented.”

**Notes for the Chapter:**

> One thing I really wanted to make clear with this chapter is that Santana is pretty much how she always is on the show: Really pissed off and combative. I wanted her to have that seething hatred even while being forced to feel and give pleasure. It's fun to write. Still it only involved oral sex.


	5. About Damn Time

**Summary for the Chapter:**

> The student finally takes Santana.

There are few things in life more satisfying than winning. Whether it’s a card game or war, knowing that in the end you were the best brings out an almost overwhelming sense of accomplishment. In this case, it’s getting the very prideful Santana on her knees. Her glare is still present, the white-hot anger in her eyes trying to burn me alive. With Brittany, I was never needlessly rough with her because she gave in so easily.

I held no animosity toward the blond and I’ve always felt kind of bad getting her mixed up in all of this. As such, I always try my best not to hurt her and I’ve done a fairly good job of that. However, I hold no such reservations with Santana. She’s generally mean to everyone, especially people like me, and her rather unique level of bitchiness has gained her an almost hated reputation at school. If it wasn’t for the fact that she’s super sexy and easy to get into bed, she wouldn’t be popular at all. She has calmed down significantly since joining the Glee club, but it’s too little too late as far as I’m concerned.

That’s why when Santana gets into position I slap my hardened dick against her face. When I see the look of surprise quickly turn to anger, I do it again even harder.

“I hardly need to explain the consequences should you be stupid enough to use your teeth.”

I lower my right hand and take a fistful of her black hair, pulling her closer until the head presses against her lips. The feel of her soft lips alone make my cock twitch just a bit. It’s an incredible feeling seeing her there, her full lips parting a little as I press against her.

“Come on, Santana, say ahh.”

Her glares at me again and opens her mouth to say something, but is abruptly interrupted when I take that opportunity to push forward and pull her head onto my cock, forcing her to take an inch into her mouth in an instant. When I try to force more inside her mouth and slide down her throat she starts gagging and pressing her hands against me. Enjoying the feeling far more than I probably should, I hold her in place with half my cock down her throat and enjoy the sensation of her throat unwillingly sucking me in.

Deciding to take at least a little pity on her, I pull my cock out of her mouth and let her go as her unrestricted airway sends her into a coughing fit. She regains her composure quickly but there are tears in her eyes.

“A consequence of trying to argue with me again. You’re my toy to do whatever I want with. I’m not interested in anything you have to say, so if you try to talk again I will simply fuck your mouth at whatever speed I wish. Understand?”

It’s obvious that she’s used to being in control during sex, and I need to be rough with her to make her realize I’m the one in charge now. She nods her head in response, most of her anger and any thought of resistance fleeing from her mind for the time being.

“A nod isn’t good enough. Say ‘Yes Master’ so we can continue.”

I take her hair in my hand again and pull her up until my cock is resting against her cheek and I look down at the beautiful cheerleader expectantly. I half-expected to see anger once again, but instead the idea of referring to me as her Master causes her to look humiliated. With my saliva covered shaft pressed against one side of her face, the look arouses me immensely. Just the first peg I’ll knock her down before this session ends. Several moments tick by and she doesn’t reply, so I pull her toward my cock again, ready to force my way in if I need to to prove my point.

“Yes Master!”

The threat works and she blurts out the words in a mixture of fear, sadness, and desperation. I look down into her eyes and still see the fire in them, that anger and pride simmering beneath the surface. Good, it’ll be boring if she breaks completely.

“Good girl. That’s what you will call me from now on. Now, how do you thank me for not punishing you?”

I keep my hand in her hair but don’t need to force either way, as she opens her mouth and sucks me inside of her own free will. The feeling of her hot mouth engulfing my shaft sends little lightning strikes of pleasure throughout my body, but I keep my eyes on her, not even trying to hide my amusement as she pleases me. In just a few moments, she swallows most of my cock down her throat and I get treated to the sight of Santana’s nose pressing near the base of my shaft.

Brittany is also very good at this, and she’s been going down on me two or three times a day for the last month, so I know what to expect. However, this is different. Brittany was merely the key to getting to Santana, so getting the ultimate prize of this entire endeavor enhances every sensation. I moan loudly in response and try so hard not to simply fuck her throat. At the moment it’s so much more satisfying allowing her to please me in her own way.

She pulls back, continuing her strong suction all the way back to the tip of my cock before releasing me completely. There’s also another reason why I’m not forcing her. She has just learned that disobedience can lead to pain, and now she’s learning that she can do things her way as long as she follows my orders. So I have no hand in it whatsoever when she lowers her head and takes one of my balls in her mouth.

“Oh fuck!”

I groan loudly and then hiss out through clenched teeth when she lets one out of her mouth only to suck in the other one. She moves her hand up and wraps it around my shaft, stroking it firmly while her mouth does wonders below. When her tongue slides over my balls it suddenly becomes a little too difficult to think, and without realizing it my grip tightens in her hair and pulls her closer until her face is pressing against my cock once again.

I only realize what I’m doing and relax my grip when Santana slides her tongue up from my balls, along the base of my shaft, and up to the tip before taking me in her mouth again. Whatever training I thought I had gone through with Brittany was quickly flying out the window and the release I thought I could hold off for a lot longer was barreling toward me. She starts a rhythm of sucking on the upper half of my shaft while stroking the lower half, her other hand playing with my balls.

“Definitely better than Brittany…”

I barely manage to choke out the words but I make sure she hears them. I can see it in her pretty eyes, she doesn’t like hearing about the girl she loves giving me head. Oh Santana, you make it almost too easy.

“She’s been sucking my cock about two or three times a day for the last month. I’m sure I don’t need to tell you how good she is with her tongue. I swear, she can get me off using just her tongue with very little effort. You can’t imagine how many times you two chatted just after she swallowed a load of my semen. While being with you, she had the taste of me in her mouth.”

Tears run down her cheeks as I continue to tell her of the things I did to Brittany. She doesn’t stop though, and I begin slowly fucking her mouth, pushing even deeper down her throat every time she sucks me in. Tormenting her like this is turning me on even more, and I thrust faster with every moment, getting closer and closer to release.

“And you know what? Tomorrow I’m going to fuck her again right on this very bed. I’ll spread her legs and slam into her, then use her over and over until we’re both exhausted. And during all of that she’ll moan loudly and come like crazy because, just like you, she likes to fuck, not make love. Even if you love her, and even if she loves you, she’s still a slut.”

It’s difficult to talk when you’re so close to release, but the enjoyment of watching her torment gives me the energy. However, that’s the full extent of my self-control, and when I feel my balls tighten up painfully I quickly pull myself out of her mouth just in time to release my semen on her face. She tries to pull away but I keep her in place with one hand while stroking my cock with the other. My mind goes completely blank and all I can do is watch and moan as thick streams of my release land on her beautiful face.

It seems like an eternity before I finally stop, and it might as well have been considering how much of her face is covered. No longer having the strength to hold her in place, I let go of her and step back until I locate the bed and sit down. Oh holy crap, I need a short breather before we continue. After a few moments I notice she’s trying to clean off her face and I stop her with a glare.

“Don’t even think about it. That’s staying right where it is until we finish.”

For a moment it looks like she’s about to argue again, but a raised eyebrow from me helps remind her of the consequences of disobedience. She lowers her hand back down to her side but it’s pretty clear that it’s immensely humiliating for her, and it doesn’t help when a bit of it slides off her face and lands on the floor. I don’t even try to prevent the smirk that appears on my face, and I just watch her for a couple of minutes until I feel I’m ready to continue. I quickly slide backwards on the bed and lay back, propping myself up on my elbows.

I motion her over to me and she reluctantly rises to her feet and crawls onto the bed. When she’s close enough I grab her and pull her body down on top of mine, cutting off her surprised gasp with a deep kiss that makes her entire body tense against mine. She responds to the kiss but it’s easy to see she’s only doing it because she doesn’t want to be punished again. Still, I’m not the only one enjoying the full-body contact. Her soft, athletic form undulates against me and her breathe increases, small gasps sharply interrupting her air intake when my hands rub up and down her slender back and then to her firm ass.

I always took a lot of time just kissing Brittany like this, enjoying the feeling of skin against skin as we made out in her bed. The feeling is intoxicating, and for the next several minutes we just get lost in it. When I finally feel like it’s been long enough, I slowly pull my lips away from hers, enjoying the long sigh that escapes her when we part. A great deal of my semen has already fallen from her face, with only a few stubborn spots remaining. I stare intensely into her eyes and slide one hand up her soft back, making her shiver.

“Fuck me, Santana. If you can do that without forcing me to make you, then you can set the pace. Otherwise I’ll just do whatever pleases me and you’ll have no control at all. I gave Brittany the same choice and she took it. As you saw in that video, she didn’t hate it.”

Santana worries at her lower lip and thinks on it for a moment before leaning up until she’s sitting on my lap, my hard shaft pressing against my stomach. She’s one hell of a sexy sight, straddling me like that. And to think, just over a month ago I was someone who would never have even the slightest chance with her. Oh how things have changed.

I respond with a favorable moan when she takes my cock in her hand and firmly strokes it up and down a few times then twists her thumb around the head, spreading precum with every swipe. My hands move to her hips, not dictating her movements but still gripping them. When she raises herself up and aligns the pointed head of my cock with her opening, I hold my breath in anticipation. I’ve been sneaking peeks at her for years, my fantasies driven by the thought of fucking her. It was always so frustrating that so many others had while I hadn’t.

I finally let out the breath I’ve been holding when she sinks down on me, slowly engulfing my cock inside of her wet channel. She grips me so tightly; I guess all that time of inactivity gave her time to tighten up more. Her breathy whimper mixes with my long groan as the last of my shaft disappears inside her. As much as I love the look of humiliation on her pretty face, I like the look of pleasure even more. As she remains motionless she closes her eyes and I watch her chest fall and she lets out a relieved sigh.

She may be a lesbian now, but she enjoyed having sex with men before. No, actually, that’s not accurate. It’s more likely she enjoyed having her pussy filled, and the fact that it was a guy doing it was just a necessary evil. I suppose that, to her, having a dildo with a mind of its own was worth it. Which is how I’m sure she’s rationalizing it right now, I’m just attached to the thing that’s making her feel good. I can live with that.

She rises back up until only the head is inside of her and then drops swiftly back down, taking me in deep and making her let out quite possibly the sexiest moan I’ve ever heard. My grip tightens on her hips, but since she’s holding up on her end, so am I, and I don’t force her movement either way. She leans forward and presses her hands against my chest, using the extra balance to start a fairly quick pace.

The feeling of her bouncing on my cock makes me grunt and groan loudly with each downward stroke, but the sight of her makes it nearly impossible to keep still, and each time she drops down I push up to meet her halfway. The sensation makes her finally open her eyes and she looks down at me, and I return her gaze as we meet again and again. Her long black hair hangs forward, just a few strands framing her beautiful features. Her mouth opens with a moan every time I slide out of her, and when our hips smack together her face tenses up with pleasure and she hisses out between clenched teeth.

Her breasts shake with each impact and I slide one of my hands up her body and palm one of her breasts, making her moan and finally break eye contact as she bends up again and removes her hands from my chest. She bends back a bit to keep her balance, but the new angle makes me enter her quite deeply, and suddenly she’s clamping down around my shaft and coming her brains out.

“Oh…oh fuck! Ahh!”

Her inner walls ripple around my cock and I have to use every trick in the book to avoid joining her. Through half-lidded eyes I watch her entire body convulse and her mouth open wide, signaling a scream of release that never quite makes it out, only sounding like a long whimper. With some effort I manage to fuck her right through her orgasm, and it’s not long before I feel her hips move to meet mine again.

“You look so incredibly hot when you come, Santana. I want to see it again. Keep riding me; use me as I use you.”

Apparently not trusting her voice, she nods and cries out sharply when I shove inside of her just as I pinch and pull on one of her nipples. Still riding the crests of her last orgasm, she sets up a rough pace, slamming herself down on my cock as I push myself up inside of her. The pleasure I’m feeling is immeasurable, and not just from the physical aspect. Knocking this bitch down a few pegs and watching her happily ride my shaft like a whore is a big part of my enjoyment.

I feel her suddenly clamp down around me again and much to her surprise I lean up, wrap my arms around her and then roll her over to her back. She doesn’t even have time to react as I press my body down against hers and start pounding away at her. Being right on the verge already, she screams out her next orgasm. Even as she squeezes me tight enough to hurt, I fuck her at a relentless pace, her athletic form sliding up and down mine with every thrust.

Every time I did this to Brittany she would completely lose all control over herself and focus on the pleasure. Santana is apparently very similar, because her legs wrap around me and squeeze with every downward thrust while her arms encircle my neck. I know that at this pace I won’t last long, and if the growing tempo of her voice is any indication she is approaching her third orgasm just as rapidly. I lean up until my lips brush her ear.

“I’m about you fill you up with my semen, Santana. I’ve been saving up a huge load just for you over the years. Every day from now on I’m going to take you again and again until you get horny just thinking about what I might do to you next. You’re going to be my own personal fuck slave, and if tonight is any indication, you’ll happily spread your legs whenever I want you to.”

I take her lips possessively in mine and kiss her hard, feeling her entire body shudder as I finish my words. Finally on the edge, I thrust forward hard three times, making her body shake against me, and muffling each sharp cry with my mouth, I finally come inside her. She joins me almost immediately, and her grasping pussy helps milk my cock of every drop of semen I have in me.

I literally feel every ounce of energy I have leave my body and empty inside of her, and her hips switch every time she feels more of my semen burst inside her body. When I finally stop coming, I stop kissing her and lower my lips to her ear again.

“Now what do you say?”

She barely manages to get her gasping voice above a whisper, but it’s clear enough for me.

“Thank you, Master."

**Notes for the Chapter:**

> And it all lead to this. I made the character a lot more of an asshole in this chapter. He finally had the sexy Santana under his control and he was enjoying it so much. This was a fun chapter to write, because lets face it Santana is hot as hell. She has always been driven more by her desires than common sense. I wanted to use that.


	6. The Game

**Summary for the Chapter:**

> The student has fun with both of the girls and plays a little game.

My fellow perverts, I will never try to deny that I’m a little screwed up in the head. It’s been a week since I finally enslaved Santana, and juggling two girls, one of whom doesn’t even know about the other, is a real chore. A chore that’s well worth it, if I do say so myself. I alternate between the two every day, and torment Santana with the knowledge that I’m fucking the woman she loves when I’m not with her. That is generating a smoldering level of animosity toward me. Since she can’t satisfy her desire to pummel me, it’s coming out when we have sex.

There is nothing gentle or slow about what we’ve been doing all week. It’s rough and at times borderline painful, but never quite reaching violent. She’s very aware that her only outlet for her anger towards me is also pleasuring me immensely, which doesn’t help her attitude at all. So she’s pretty much in a no-win situation and the only thing she’s getting out of it is one powerful orgasm after the next. To put it simply, we’re using each other and I’m experiencing the most intense sex of my life.

But don’t get me wrong, I’m also enjoying the slower, far gentler sex with Brittany. With her I can just take my time and enjoy a slow build up to release. And whenever I can, I record these sexual acts, getting every sordid experience on video. It’s gotten to the point where I’m pretty secure in my control over them and it’s about time I move on to the next phase, which unfortunately includes letting Brittany know about Santana.

My main method of control over her was my threat of outing her best friend, so there’s no telling how she’ll react when she discovers her sacrifice was more or less for nothing. I knew I had to think things through very carefully and delicately plan a way to let the blond know while minimizing any risks. After a full week to think about every little detail, I came up with the perfect idea. The result of that idea is Brittany walking into her room and catching Santana deep throating me on her bed.  
Okay, so maybe I define subtlety differently! The Band-Aid is now off, and that’s all that matters in the end! The absolute best part is that I didn’t tell Santana about it at all, so when the blond cheerleader walks in on us, she has half my shaft down her throat. The sight of Brittany startling her, she tries to rise up off my cock but I stop her with my hand in her hair, holding her in place. I look over at the stunned blond and smile.

“Hello, Brittany. Get over here and get on your knees. Now!”

She responds almost automatically to my firm command, I’ve been training her for a full month after all, and joins her best friend on the floor in front of me. I let go of Santana but before she can pull herself off I fix her with a glare.  
“Keep sucking. If you stop at all then I’ll make her take your place.”

The glare she shoots at me could melt steel, but she does as she’s told and starts bobbing her head again. Although I’m able to react calmly, it still takes a lot of effort to talk. Santana is almost mind-numbingly good at sucking dick, and she’s only gotten better from all this practice. After I make sure that she’s going to continue pleasuring me, I return my focus to Brittany.

“Allow me to give you the nutshell version, Brittany. I told your best friend about how much you’ve sacrificed to keep her secret. Because she cares about you so much, she agreed to become my own personal sex slave, just like you. She’s the main reason why you’ve had every other day to yourself for the last week. She takes care of me when you can’t.”

Throughout my explanation, Brittany stares at her best friend in surprise and not a little bit of sadness. She was following my orders to keep her best friend safe, after all. She’s been forced to cheat on a boyfriend who adores her, and I’ve taken no small amount of pleasure in making her feel like the slut that she’s been trying to change about herself.

“But she hasn’t been entirely unwilling. Get this girl angry with no outlet and she’ll fuck your brains out. It’s kind of touching what people will do for love. I’ve fucked her even harder than I have you, Brittany, and she keeps coming like she hasn’t had a good lay in years. Look at her now, sucking my dick to protect you, while just yesterday you were doing the same to protect her.”

Tears began to stream down Santana’s cheeks and she stops moving, so I take her head in my hands and start moving her up and down my cock. I purposely let out a loud moan as her nose presses against the base of my cock. Brittany is getting visibly more and more upset watching her friend do this and looks up at me.

“Why are you doing this?”

I laugh in response and then finally slip my cock out of Santana’s mouth, allowing the girl to breathe as I smile down at them.

“Part of it is because it feels good. You’re both incredibly hot and really good in bed. Up until just over a month ago I didn’t have any chance with either of you, but now I get to fuck you whenever I want.”

I reach down and slide my hand beneath Brittany’s shirt, running my fingers down her smooth stomach then back up to squeeze one of her bra covered nipples. Brittany is the kind of girl who is always horny, so you can get her started with very little effort. I look over at Santana, who is clearly not enjoying the sight of me touching the woman she loves. Knowing I’m doing it is one thing, but watching it is quite another.

“But the main reason is because of her. People who are afraid to be what they really are piss me off. If she’d been open about her sexuality right from the start, I never would have found the leverage I needed to begin all of this. Now it no longer matters, because I have enough material on the two of you to ensure an entire lifetime of sexual slavery to me. I’m a horny teenage boy with two smoking hot cheerleaders taking care of my needs; of course I’m going to make use of you.”

Pulling my hands out of her shirt, I order her to remove all of her clothes and get back in position, then watch her do so while I rub my shaft against Santana’s face. My eyes are drawn to the athletic blond, and not for the first time I admire her body as more of it is exposed to me. When her clothing is removed she drops to her knees between my legs again and I slap my cock against Santana’s face once more before pressing the tip against Brittany’s mouth.

“Go ahead and show her how good you are.”

Brittany hesitates and looks at her distressed best friend. It’s clear, to me at least, that the last thing Santana wants to do is watch the woman she loves pleasure me. The blond turning back to me and sucking the head of my cock inside her mouth is a good way to remind her that there is no real choice in the matter. I look down into the blonde’s pretty eyes and groan as she takes most of my cock down her throat within just a few seconds.

The tears are flowing from Santana again, but I place a hand behind her head and pull her closer until her cheek is pretty much rubbing against her friend’s, getting the perfect view of her pleasuring me.

“I’m sure I don’t know to tell you this, Santana, but Brittany is way too good with her mouth. Even if I only used her mouth every day, she would still drain me dry. There’s just something about her that makes it so much fun to watch her do it too. She’s probably spent more time with my cock inside her mouth instead of her pussy.”

I know I’m tormenting them both, but Santana even more so. It’s immensely satisfying to look down and see both my girls on their knees before me. My arousal keeps shooting through the damn roof and I struggle to maintain control over myself.

“Help her out, Santana. The sooner I come the sooner you get to stop watching her pleasure me.”

I let go of her head and allow her to move, then nearly embarrass myself and come immediately when the dual sensations of one mouth around my cock and one licking my balls makes my entire body shudder. Pulling on some deep, lesser-known reserves of willpower I somehow manage to hold off, but having two skilled mouths pleasing me keeps me right on the edge.

Without even needing to tell them to, they suddenly switch and Santana’s mouth deep throats my throbbing shaft while Brittany changes tactics and sucks on one of my balls. Without any previous experience with a double blowjob, I literally have to fight my body to prevent my release. Despite my constant moaning and shifting, I don’t take my eyes off the girls, instead making sure they know I’m watching.

“Stop sucking, both of you just use your tongues. When I tell you I’m about to come, one of you better have your lips around my cock ready to suck it down.”

I can’t help myself; I’m experiencing every man’s fantasy right now. They immediately do as they’re told, but they both have a small look of determination. Both of them want to stop the other from being forced to swallow my semen, so they’re both going to try. Neither of them wants to, but both of them will try. I won’t lie, at this moment I love my life.

Having two very talented tongues on my shaft nearly makes me hyperventilate. They both take turns running their tongues up and down my cock, with the one waiting circling her tongue around the sensitive head. Knowing that the person who wins will have a much likelier chance if she’s closer to the tip of my cock, I wait until Brittany is licking the head before I warn them. Santana isn’t nearly fast enough and in a split second, the blonde is shoving every inch of me down her throat.

I manage to smirk down at Santana and wind a hand in Brittany’s hair, holding her down on me as I moan loudly and come down her throat. She already has plenty of experience with this, and expertly swallows my semen and milks my shaft. Santana watches as her best friend’s throat expands while she drinks down every drop.

I feel energy leave my body with each shot of come, and when I finally stop I pull Brittany off my cock and struggle to pull in oxygen. While resting, I quickly think up the next part of my plan. To be honest, and I know I’m going against my golden rule here, I didn’t entirely think the next part through. Despite everything I’ve experienced over the last month, it’s completely new to me.

But it’s necessary to my grand scheme if I also want to bring another person into this.

“Santana, lay back on the bed and spread your legs.”

I guess she incorrectly assumes I’m going to fuck her instead of Brittany, because she obeys without complaint. When her head rests on the pillows I stand up and push Brittany onto her hands and knees at the edge of the bed, actually not too far away from Santana.

“We’re going to play a game. You see, Brittany has told me a lot about your relationship over the last month. Fascinating stuff, really. I especially liked the part where she told me that the person who took her anal virginity was you.”

I absentmindedly rub my hand against Brittany’s firm, lovely ass and smile at Santana.

“Not only that, you’re the only one who has ever taken her anally. It’s like your own sacred spot, a piece of her only you can ever have. I genuinely think that’s kind of sweet. You both sleep around but you reserve something that’s just for the two of you. I like that, as weird as it is. Another surprising detail is that you haven’t lost yours.”

Santana apparently doesn’t like where this is going, because she’s staring at me in disbelief, a slight shake to her head as she silently begs me not to do what I want to do. I’ll be perfectly honest with you, even the cold exterior I’m trying very hard to keep up melts significantly when I see the look on her face. I think I’ve mentioned this before, but I’m kind of a romantic. I can certainly understand wanting to have a piece of someone that nobody else gets to experience. I quickly revise the game in my head.

“So here’s the game. I’m going to fuck Brittany, there’s just no way around that. If she makes me come first, then I get to have your anal virginity and you get to have her ass all to yourself. However, if I make her come first, then I fuck her ass right here in front of you. Now here is where you come in. If you can make yourself come three times before I do just once, then I get to take you both anally, but she gets your anal virginity and not me. Of course, that only applies if she makes me come first.”

You can officially file me under “Right Bastard” and be done with it. The original plan was just fo fuck Brittany anally and put her in a position where she’ll need to make me come in front of Santana so I won’t take her best friend’s anal virginity.

With these new rules, Santana can only aim for an outcome that results in me having both of them. The last thing she wants if for me to take Brittany anally, but she also doesn’t want me to have her anal virginity either. To get even a little bit of what she wants, she’ll have to sacrifice her virginity to me or sacrifice Brittany to me. I’m not an idiot, she’s a woman in love. If Brittany loses or wins, either way, the outcome is a lot worse. However, if Santana manages to win, then she gets something in the middle. Nothing great, but nothing terrible either. She has no real choice except to win this herself.

As for Brittany, she has even less of a choice. The only good option for her is to make me come first. Whatever the outcome, I’m going to have a lot of fun. I walk up behind Brittany and rub my shaft between her legs, brushing up against her sensitive clit. Her loud gasp seems to motivate Santana even more.

“Do you both understand the rules?” They both nod, “Good, now let’s begin.”

Wasting no time, I push forward and quickly bury my entire length inside Brittany’s tight pussy. I can never get used to how good it feels, or how erotic it sounds, when she grips my shaft within her and cries out sharply from the penetration. She seems stunned for a few moments and I’m able to pull almost all the way out and enter her deeply again twice before she remembers her role in this.

She braces herself against the bed and starts pushing back against me, her ass smacking loudly against my hips as she meets me part way. I’ve learned that Brittany loves just about everything about sex. She loves the sound of it, the groans and moans, of skin smacking against skin. She loves the feeling of losing control of herself and just bathing in the all-consuming pleasure of something buried deep inside of her. Get her started and she leaves the entire world behind.

I look up from the tantalizing view of her back flexing each time I push inside of her, and check on Santana. Without anything else to look at, and apparently finding it impossible to close her eyes, she has nothing but a view of the woman she loves getting fucked by me to pleasure herself to. Knowing she has to make herself come three times, one hand pinches and pulls on her nipples while the other hand furiously pushes two fingers in and out of her dripping pussy, stopping every once in a while to thumb her clit.

It’s one hell of an erotic sight, and when I notice that Brittany’s head is hanging down, I give her firm ass a hard slap to get her attention.

“Watch Santana pleasure herself. Don’t take your eyes off her no matter what.”

Not having even the slightest desire to disobey, Brittany raises her friend and stares at her friend, both of them getting a full view of each other’s pleasure. Santana looks sexy as sin masturbating, and I know from experience that Brittany’s facial expressions are always intense when she’s having sex.

Although I’ve always felt guilty getting Brittany involved in this, I can’t deny the fact that she’s one hell of a lay, and I would have been missing out if I had chosen not to include her in my plans. Even overcome with her own pleasure as I ram away at her, she clamps down around my cock each time I enter her and it’s almost tight enough to stop me completely. It’s the perfect way to milk my cock, and she knows how much it drives me crazy.

I have no intention of coming until Santana reaches her three orgasms, and the training I’ve done over the last month has given me the gift of being able to hold my release off for a while. Brittany has that ability as well when she’s determined, and right now neither one of us are close to blowing it.

I focus on Santana again when her moans reach a higher pitch and I watch her entire body shudder as she comes for the first time. I’m not worried about her faking it at all. Santana can do a lot of things, but she can’t fake an orgasm worth a damn, and trust me she has tried. I smirk when I notice that she doesn’t take her eyes off Brittany during climax.

Deciding to alter the angle of penetration, I bend forward and grab her swinging breasts in my hands, squeezing the firm globes between my fingers and tweaking her nipples.

“Oh shit! Ahh!”

Brittany curses loudly and then cries out as I ram into her, the new angle and extra attention to her body apparently quite welcome. She tightens around my shaft and closes her eyes, a hiss between her clenched teeth telling me she’s fighting off an orgasm. Not wanting to push her over that edge, I get her several moments to control herself before I start moving again, each thrust making the beautiful blond moan in pleasure.

I must admit, it’s insanely difficult for me to keep control as well. I have the added benefit of the earlier orgasm taking the edge off, but Brittany knows exactly how to pleasure me.

“Please, fuck me harder! I’m so close!”

Damn her! I’ve always enjoyed the sound of her voice during sex, and she knows that. Apparently she wants to torment me, even though we’re all aiming for the same outcome.

I watch as Santana fingers herself to another orgasm, now only one away. I try to laugh at her, but it only comes out as a cough when Brittany chooses that moment to beg me to come inside of her.

“As much as you claim to hate me for fucking Brittany, you really seem to get off on watching us do it.”

Santana glares at me, but it’s hard to take her seriously when she’s masturbating and moaning at the same time.

I suddenly straighten up and grip Brittany’s hips in my hands, then lift her up so I can push her fully onto the bed. When I’m done repositioning her, her face is only a few inches away from Santana’s. Not wanting to break the pace any longer, I resume ramming my way inside of her.

Brittany can’t hide her pleasure even if she tries, and when she opens her mouth and lets out a loud groan, Santana takes that opportunity to lean forward and kiss her. Santana’s right hand moves up behind the blond’s head and pulls her into the passionate kissing, eliciting a moan from the surprised, but happy cheerleader. Her other hand speeds up between her legs, quickly approaching her third orgasm.

Not wanting to disrupt the kiss, and to be honest I don’t hate the view, I slow down my pace so her entire body doesn’t move with the impact of my thrusts. It’s not long before Santana finally reaches orgasm again, whimpering into Brittany’s mouth as her entire body shudders. The sight of the two cheerleaders kissing, not to mention the sensations I’ve endured so far tonight, I can feel my own release right on edge of a long cliff.

When Santana pulls out of the kiss, Brittany lets out a long moan and shudders, but manages to hold off her own climax somehow.

“I love you, Brittany.”

I barely hear her whisper it, but Brittany smiles at her friend.

“I love you, too.”

Perfect!

The fact that I need to come right after such a nice moment is purely coincidence, but I don’t hear any complaints. I grip her shoulders in my hands and pull her back as I push forward, non-too-gently burying my cock inside of her as deep as I can and shooting my semen inside her body.

Brittany curses loudly in response and her loud moan signals her own release, her entire body convulsing as pussy ripples around my shaft, milking me of every drop I have. I knew I wouldn’t be able to try anal sex that night, but I have plans for that later.

When we both finish coming, I pull out of her and smile when she lays down beside her best friend to recover her strength. Taking in the sight of the two beautiful girls laying side by side, I almost forget the next part of my plan. It’s utterly impossible to completely forget it however, since there is picture of my next plan beside Brittany’s bed.

“Okay, you two have one last thing to do before I leave.”

I cross the bed and pick up said picture, showing it to the girls.

“I want you to tell me everything you know about Quinn Fabray.”

**Notes for the Chapter:**

> This chapter was way too much fun to write, although the idea of the game was quite simple. I just can't get over the mental image of having both of them at once. This was the chapter where I finally decided to add Quinn to the fun sometime in the near future. I felt like a real bastard writing some of it though. XD


	7. Epic Quinn

**Summary for the Chapter:**

> The student spies on Quinn during a private moment.

It became pretty clear right from the beginning that I couldn’t use the same methods against Quinn that I used on Santana and Brittany. First off, if the information I got from the two of them is anything to go by, the three of them are good enough friends to hang out together, but not so good that I could use Santana’s secret as leverage against her. Secondly, compared to the other girls, Quinn is practically a saint. She doesn’t seem to have anything embarrassing that I can hold over her head.

When I started all of this in order to gain control over Santana, I was at least somewhat secure in the knowledge that I would have not only the woman she loves, but her secret as a means of control. Even if by some small chance I failed to sexually blackmail the bitchy cheerleader, I could at least insure her silence of the attempt anyway, keeping myself safe in the process.

Truth be told, Santana’s secret isn’t even my number one method of control anymore. Everything I need to keep both her and Brittany subservient is in the videos I made after the fact. I needed to think of a way to get Quinn in a compromising situation that would allow me to gain just enough control to push things forward. I couldn’t just rush into it, I had to plan, because one bad move could ruin everything for me, and I was in no hurry to end my fun with the two beauties.

I must have gone through a dozen different plans before it finally dawned on me: Delegation.

It wasn’t difficult to convince Santana into carrying out certain instructions for me. She came right out and told me that she didn’t care stabbing her friend in the back because she’s tired of Quinn doing really shitty stuff and somehow getting away with it.

I’m no idiot, I know that any kind of strong emotion, in this situation that emotion being anger, should not be quelled, but focused. Santana is angry about being seen as the bitch, when Quinn is seen as perfect despite doing much worse things. I suppose I could understand that, but either way it gave me an opening.

For weeks, Santana acted not only as my eyes and ears, but my mouth as well. I knew that the best way to make use of the opening was to mess with Quinn’s state of mind. Most people would approach this situation by destroying her support structure, namely her relationship with her friends. If I actually had anything against Quinn, I might have done just that, but I don’t. There’s just something so brutish about that method.

I took it a step further and played upon something that was natural to her already: Curiosity.

Quinn is a very curious girl. Santana told me that Quinn always quite attentively listened when she bragged about her sexual exploits in the past, even after she became pregnant. It wasn’t difficult to give Santana new tales to tell her best friend, and with every erotic story I planted ideas in her head without ever speaking to her.

I always had Quinn figured as more of a sexual creature than she lets on, but it was also obvious that her unexpected pregnancy did a lot to stifle her urges. It’s kind of like she placed a wall between her personality and her desires, and with every tale I was slowly chipping away at that wall. Even Santana could tell the blonde was sexually repressed.

Then came the time when I traded a pickaxe for a canon. Under my instructions, Santana forgot her personal laptop at Quinn’s house one night. It was pretty late by the time she noticed it, and just as I thought she would she turned it on and laid on her bed. I didn’t have to create something to use against her, just foster what was already there. It didn’t take her long to find what the video Santana and I created.

Unknown to her, the laptop’s built in webcam turned on the moment she started hitting keys, and I saw the entire thing when her eyes widened in shock at the sight of her best friend deep-throating my cock. When I had decided to take the next step, I made a video of Santana giving me a blowjob that very day. She was still noticeably unhappy about it, at least to me, but I guess the knowledge that it would lead to knocking Quinn down a peg made her very enthusiastic.

Since I started blackmailing her, I’ve received so many blowjobs from the cheerleader that I lost count, but let me tell you, when she’s really into it there is no possible chance of holding back for long.

I had the camera pointing down at her face, concealing my identity and giving Quinn a full, HD view of Santana’s considerable skills. At the time I remember wishing I had just used a tripod to keep the camera steady instead of holding it in my hands, because the enthusiastic way Santana sucked every inch of my shaft made it impossible to keep it completely steady.

Watching the beautiful blonde through the webcam was quite a sight to behold. She stared, transfixed at the video, her mouth open just a bit, and her breathing increased more as the video went on. It was pretty late, and she had already removed her bra, because her nipples hardened and pressed against her white top. I watched her pretty eyes as she watched the erotic scene in front of her noticing every small reaction to what happened. I could just say its research into knowing what goes through her head, but I just really like her eyes.

Quinn suddenly shifted into a more comfortable position on her back, propping her head on a couple of pillows and resting the laptop on her stomach. This gave a much better look at her face, and her nipples pressed even tighter against her top.

Since the laptop was resting on her stomach, I couldn’t see it as her hand reached down between her legs and slipped inside her pants, but I could certainly hear it. The rustling of fabric was followed by her breath hitching for just a second, and her pretty eyes closed for a few moments until she let out a long sigh. When her eyes opened again to watch the video, they had that sexy, glazed-over look that I’ve seen so many times on Santana and Brittany.

When her breathing became heavier it was incredibly obvious what she was doing and an image of Quinn fingering herself flashed through my mind. I kept my eyes on her; however, taking note of every twitch and gasp as her fingers invaded her pussy and brought a long moan out of her.

In the video, Santana dragged her sucking lips up my cock and then lowered her mouth to my balls, taking her time to suck each one into her mouth while her hand worked up and down my glistening shaft. This seemed to surprise Quinn, and she stared intently as her best friend paid loving attention to my balls. Her movements between her legs only seemed to increase in speed, until I could definitely hear it.

The intense look of arousal on Quinn’s face was hypnotizing, and my attention was only drawn away from her beautiful features when her free left hand rose up and tweaked her right nipple through her top. She moaned out a sexy little whimper and did it again to the other nipple, making me lick my lips with the desire to take them into my mouth when her back arched up just a little from the bed in response before settling back down.

I know it’s unlikely that Quinn has any sexual attraction to Santana, and if she does it is probably hidden deep, but you can still watch a scene like the one playing out in front of her and find it erotic enough to masturbate to. Quinn isn’t a virgin, but she’s about as close as you can get without actually being one. Santana told me that the blonde’s single sexual experience hadn’t been much of a complete one. She didn’t get to try other things before Puck was inside of her, and after that she never got the chance to explore her sexuality.

Everything I wanted to try, I’ve been able to with Brittany or Santana. I’m able to explore my sexuality, while Quinn has put up a wall that denies her the ability to try. It really does fascinate me, as well as arouse me, as I watch this minimally experienced girl pleasure herself.

In the video, Santana returned her mouth to my cock and sucked it down her throat again.

“Touch yourself,” I tell her in the video, catching Quinn’s attention.

I knew that if the video could arouse Quinn enough to make her masturbate, then throwing some words into the video that has to do with that very act would get her more involved, even if it is within her own mind. By making the aroused girl connect with the words, it’s a very short trip to connecting with the person on the screen. Quinn doesn’t even know me, so she can’t place the voice to an identity, in a sense allowing her to imagine whatever guy she wants.

You’d be surprised to know how easy it easy to make someone see one thing while imagining another, especially while they’re aroused. As she continued to watch the video, she began to wonder what it would be like to take Santana’s place. Her curiosity makes it so easy to just imagine what it would feel like to masturbate while giving a guy a nice, deep blowjob.

She suddenly moved the laptop aside for a moment, moving out of view of the camera for a short time before returning to watch the video, this time lying on her side with the laptop on the bed and not a single stitch of clothing on. I drank in the sight of her sexy, lithe form and memorized every inch I could see, which was pretty much everything from the front.

Her breasts aren’t big, which I hear is quite an annoyance for her, but I think they fit her body well. They’re capped by the most delicate nipples I’ve ever seen, small but hard and just begging to be sucked on. Her flat stomach is perfectly toned from her athletic lifestyle, and if I didn’t already know, I never would have guessed she’d given birth. She has those hips that look really sexy, like you could just grab on to them and pound away, and she was made complete by long, smooth legs. I couldn’t see much between her closed legs, but I didn’t notice a single patch of hair, probably routinely shaved.

Quinn props her head up with one hand, watching the video while her other hand snakes between her legs to return attention to where she wanted it most. With her full body in view, I became the one transfixed, and couldn’t stop watching her even if I wanted to.

In the video, Santana was touching herself, masturbating for the camera and moaning around my shaft. Quinn’s hips moved back and forth against her fingers, her eager digits prodding her aching clit. Whatever was holding her back before seemed to have completely vanished because her loud breathing kept being cut off by long and utterly sexy moans. Her mouth stayed open except when her teeth worried at her lower lip and her hips jerked when she touched herself in just the right way to send pleasure arching through her lithe body.

I almost didn’t see it happen, but when her hand lowered just a bit further, she pushed a finger inside of her neglected pussy and started to thrust it in and out.

“Good girl,” I say in the video, a complete coincidence, “Push them in as deep as you can.”

Santana nods in the video, but Quinn actually seems to respond to it. Another finger joins the first, and with a whimper of delight she pushes them all the way inside. Only waiting a few moments to enjoy the feeling, she then starts to fuck herself with her fingers. That’s the only way to properly describe it, because there’s nothing gentle about it. The sexy blonde seems determined to reach her orgasm.

Her entire body seems to shift back and forth as her fingers plunge in and out of her, but her pretty eyes never leave the screen for more than the time it takes for her to close her eyes and moan in pleasure. In the video, Santana was doing a remarkable job of giving me an incredible blowjob and fucking herself at the same time. At that point in the video, I was way past the point of no return, and I had already given Santana instructions on what to do next before starting the recording.

Quinn watches in fascinated arousal as I give a quick warning to Santana and suddenly release down her throat. Even with her experience, Santana couldn’t swallow the amount that her mouth was suddenly filled with, but still bobbed her head up and down my shaft while it leaked out of her mouth and coated her chin. My moans at release were very vocal, and the sight and sound of it pushed Quinn right over the edge.

I was then treated to a sight only one other had seen: Quinn Fabray having an orgasm. Her eyes closed and her mouth opened in a scream of pleasure that rocked her entire body. Her fingers sped up as her orgasm approached and then buried themselves as deep inside her as possible just before her pussy clamped down around them like a vice and she came her brains out.

I had been with both Santana and Brittany on multiple occasions, yet I can say without a doubt I had never witnessed anything as sexy as Quinn having an orgasm. It seemed to take forever before her hips stopped shaking and her body relaxed, but when it did she rolled over onto her back and slid both hands up her now sweating body to give her breasts a quick squeeze, earning another groan from the pleased cheerleader before she relaxed against her bed and tried to regain her energy.

It took all of five seconds before I started solidifying my plans to make her mine.

**Notes for the Chapter:**

> The original idea I had for this and the actual finished chapter are different on every level. In the original version he was supposed to use a videotape Santana has of Quinn joining both her and Brittany in a one time threesome. He would then blackmail her with the tape and add yet another girl to the fun. However, I didn't like using the same kind of blackmail twice.
> 
> So instead I came up with an idea to mess with Quinn's head. I wanted to put her in a situation where she would have sex with the student through manipulation of her friends and not blackmail. This chapter was the start of that. Also, the mental image of Quinn pleasuring herself is way too juicy to ignore.


End file.
